1. Field of the Invention
This invention relates to a new process for preparing organic fluorine-containing compounds. More particularly, it relates to a process for replacing a hydroxyl group in organic compounds with a fluorine atom and/or the oxygen atom of organic carbonyl compounds with two fluorine atoms by reaction of the hydroxyl or carbonyl compound with a dialkylaminosulfur trifluoride.
2. Description of Prior Art
Several materials have been used in the past as fluorinating agents. The use of sulfur tetrafluoride is disclosed in U.S. Pat. No. 2,859,245 and 2,983,626. W. C. Smith, Angew. Chem. 74, 742 (1962) presents a review of its use. W. A. Sheppard, J.A.C.S. 82, 4751 (1960); 84, 3058 (1962) describes the use of phenylsulfur trifluoride. "Fluoroamine reagent", (CH.sub.3).sub.2 --NCF.sub.2 CFHCl, has also been used. All of these reagents are not completely satisfactory for one reason or another.
The dialkylaminosulfur trifluorides have been previously reported in the literature but no mention has been made of their use as fluorinating agents. The following are mentioned:
1. G. C. Demitras, R. A. Kent and A. C. MacDiarmid, Chem. Ind. (London), 1964, 1712; and G. C. Demitras and A. G. MacDiarmid, Inorg. Chem., 6, 1903 (1967). These papers describe the preparation of (CH.sub.3).sub.2 NSF.sub.3 by the reaction of SF.sub.4 with (CH.sub.3).sub.2 NSi(CH.sub.3).sub.3. The .sup.19 F nmr spectrum was described.
2. S. P. Von Halasz and O. Glemser, Chem. Ber., 103, 594, (1970), show the preparation of (C.sub.2 H.sub.5).sub.2 NSF.sub.3 by reaction of (C.sub.2 H.sub.5).sub.2 NSi(CH.sub.3).sub.3 with SF.sub.4. This compound reacts with (CH.sub.3).sub.3 Si--N=C=N--Si(CH.sub.3).sub.3 to give NCN=SFN(C.sub.2 H.sub.5).sub.2. No other chemistry is reported.
3. S. P. Von Halasz and O. Glemser, Chem. Ber., 104, 1247 (1971), describe the preparation of RSF.sub.3 (R = Me.sub.2 N, Et.sub.2 N and piperidino) by the reaction of R--Si(CH.sub.3).sub.3 with SF.sub.4. No fluorination reactions are disclosed.